Why Discomfort in Investment Banking Can Be a Signal of Fit—not Failure

Scott Galloway’s journey illustrates a counterintuitive path from rejecting investment banking to building a robust career founded on business, teaching, media, and investing. His early talent for entering Morgan Stanley post-UCLA placed him squarely within one of corporate America’s most arduous environments, yet he admits he was “terrible at it” [7]. This admission demonstrates a rare form of professional humility and suggests that recognizing limitations early can be a key driver toward reorienting one’s trajectory.

From a strategic perspective, Galloway’s situation underlines the value of form over prestige: while investment banking holds high status, what truly matters is the skills and mindsets cultivated there—precision, stamina, navigating ambiguity. Galloway turned the discomfort of that environment into clarity about his aptitudes, leading him toward entrepreneurship and teaching, where he perceives himself more effective.

Rejecting “passion” as primary career advice also functions as a wake-up call. Galloway argues it’s often advice given by people who already have freedom and choice. For most people, he contends, the path is more iterative: engage in different roles, notice where growth and satisfaction intersect, then lean into that. The strategy is resilient: it copes with volatility, and allows pivoting enough to capture outsized upside.

From the investment banking perspective: his story is instructive both for professionals and for firms. For individuals, the lesson is to know your temperament: do you excel in high-pressure, formulaic, rigid environments, or do you thrive when you’re innovator, builder, mentor? For firms, the implication is to recognize that not all high potentials are suited to long careers in banking; some will leave early—but this shouldn’t be treated as failure but as one possible outcome of career design.

Open questions for professionals or students inspired by his arc include: What proportion of early career discomfort is essential versus avoidable? When is quitting a sign of maturity versus giving up prematurely? And how can corporate cultures better support employees who are learning that they may belong elsewhere?